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Issue 39, 2013
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A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

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Abstract

The development of multistep continuous flow reactions for the synthesis of important intermediates for the pharmaceutical industry is still a significant challenge. In the present contribution the biaryl-hydrazine unit of Atazanavir, an important HIV protease inhibitor, was prepared in a three-step continuous flow sequence in 74% overall yield. The synthesis involved Pd-catalyzed Suzuki–Miyaura cross-coupling, followed by hydrazone formation and a subsequent hydrogenation step, and additionally incorporates a liquid–liquid extraction step.

Graphical abstract: A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

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Publication details

The article was received on 16 Jul 2013, accepted on 12 Aug 2013 and first published on 14 Aug 2013


Article type: Paper
DOI: 10.1039/C3OB41464G
Citation: Org. Biomol. Chem., 2013,11, 6806-6813
  • Open access: Creative Commons BY-NC license
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    A three step continuous flow synthesis of the biaryl unit of the HIV protease inhibitorAtazanavir

    L. Dalla-Vechia, B. Reichart, T. Glasnov, L. S. M. Miranda, C. O. Kappe and R. O. M. A. de Souza, Org. Biomol. Chem., 2013, 11, 6806
    DOI: 10.1039/C3OB41464G

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